Ethanol → Ethyl 1-azabicyclo[3.3.1]nonane-5-carboxylate

Participants

Reaction Steps

A mixture of 1-benzyl-5-(ethoxycarbonyl)-1-azoniabicyclo[3.3.1]nonane bromide (932 mg), 10% Pd/Carbon with a 50% hydration (25 mg), and EtOH (15 mL) was stirred at room temperature under a hydrogen atmosphere of 3 atm. The reaction mixture was filtered through Celite and the filtrate was concentrated under reduced pressure to obtain a colorless solid. To this solid were added CHCl3 and a saturated aqueous NaHCO3 solution, and the organic layer was separated. Furthermore, the aqueous layer was extracted with CHCl3. The organic layer was collected, dried over MgSO4, and then concentrated under reduced pressure to obtain ethyl 1-azabicyclo[3.3.1]nonane-5-carboxylate (376 mg).

Provenance & Evidence